Thionyl Chloride → 2-(Chloromethyl)-4-fluoro-1-methoxybenzene

HRID 2110246Notes

Reaction equation

HRID 2110246 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH3:11])=[C:6]([CH2:8]O)[CH:7]=1.S(Cl)([Cl:14])=O>ClCCl.CN(C=O)C>[Cl:14][CH2:8][C:6]1[CH:7]=[C:2]([F:1])[CH:3]=[CH:4][C:5]=1[O:10][CH3:11]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 22014996(5-Fluoro-2-methoxyphenyl)methanol

Product 1

HCID 3026862-(Chloromethyl)-4-fluoro-1-methoxybenzene

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

19.0 g (0.12 mol) of (5-fluoro-2-methoxyphenyl)methanol are dissolved in 105 ml of dichloromethane. One drop of DMF is added, and 26.6 ml (0.37 mol) of thionyl chloride are then added slowly. The solution is stirred at RT for 2 hours and evaporated under reduced pressure. The residue is taken up in ethyl acetate, the mixture is cooled and admixed with water and then washed with saturated sodium bicarbonate solution and water, dried over magnesium sulphate and evaporated under reduced pressure.

Workup

  1. customevaporated under reduced pressure
  2. temperaturethe mixture is cooled
  3. washwashed with saturated sodium bicarbonate solution and water
  4. dry with materialdried over magnesium sulphate
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-abca08c2ab0e404dbf5f2fbbfbd55f7c
Source dataset
uspto-grants-2009_04
Patent number
US07517896B2

Reaction notes

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